Expeditious synthesis of N-bridged heterocycles via dipolar cycloaddition of pentafulvenes with 3-oxidopyridinium betaines |
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| Authors: | Jinesh M KuthanapillilSreeja Thulasi Rani RajanK Syam Krishnan E SureshKV Radhakrishnan |
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| Institution: | a Organic Chemistry Section, Chemical Sciences and Technology Division, National Institute for Interdisciplinary Science and Technology (C.S.I.R.), Trivandrum 695 019, India
b Analytical Sciences Discipline, Central Salt and Marine Chemicals Research Institute, Bhavnagar 364 002, India |
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| Abstract: | A new and highly versatile approach towards the synthesis of bicyclo6.3.0]undecanes and bicyclo5.3.0]decanes was accomplished. The methodology adopted involved 6+3] and 3+2] cycloaddition reactions of pentafulvenes with 3-oxidopyridinium betaines generated either by the action of a base on the pyridinium salt or thermally from pyridinium betaine dimer. These well-functionalized bicyclo6.3.0]undecanes and bicyclo5.3.0]decanes offer a wide range of synthetic options, which can be expected to translate into a variety of rapid and efficient synthesis of natural products. |
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| Keywords: | Pentafulvenes Cycloaddition 3-Oxidopyridinium betaines Bicyclo[6 3 0]undecanes Bicyclo[5 3 0]decanes |
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